EP2906574B1 - Gemisch aus verschiedenen unsymmetrischen bisphosphiten und dessen verwendung als katalysatorgemisch in der hydroformylierung - Google Patents

Gemisch aus verschiedenen unsymmetrischen bisphosphiten und dessen verwendung als katalysatorgemisch in der hydroformylierung Download PDF

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EP2906574B1
EP2906574B1 EP13773210.3A EP13773210A EP2906574B1 EP 2906574 B1 EP2906574 B1 EP 2906574B1 EP 13773210 A EP13773210 A EP 13773210A EP 2906574 B1 EP2906574 B1 EP 2906574B1
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compounds
mixture
mixture according
reaction
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EP2906574A1 (de
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Andrea Christiansen
Robert Franke
Dirk Fridag
Dieter Hess
Katrin Marie DYBALLA
Bernd HANNEBAUER
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Evonik Operations GmbH
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Evonik Degussa GmbH
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
    • C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
    • C07F9/6574—Esters of oxyacids of phosphorus
    • C07F9/65746—Esters of oxyacids of phosphorus the molecule containing more than one cyclic phosphorus atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide
    • C07C45/50—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide by oxo-reactions
    • C07C45/505—Asymmetric hydroformylation
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J19/24—Stationary reactors without moving elements inside
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0201—Oxygen-containing compounds
    • B01J31/0209—Esters of carboxylic or carbonic acids
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
    • B01J31/0235—Nitrogen containing compounds
    • B01J31/0237—Amines
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
    • B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
    • B01J31/0271—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds also containing elements or functional groups covered by B01J31/0201 - B01J31/0231
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/18—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms
    • B01J31/1845—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes containing nitrogen, phosphorus, arsenic or antimony as complexing atoms, e.g. in pyridine ligands, or in resonance therewith, e.g. in isocyanide ligands C=N-R or as complexed central atoms the ligands containing phosphorus
    • B01J31/185—Phosphites ((RO)3P), their isomeric phosphonates (R(RO)2P=O) and RO-substitution derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/49—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide
    • C07C45/50—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with carbon monoxide by oxo-reactions
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/36—Preparation of carboxylic acid esters by reaction with carbon monoxide or formates
    • C07C67/38—Preparation of carboxylic acid esters by reaction with carbon monoxide or formates by addition to an unsaturated carbon-to-carbon bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
    • C07F15/0073—Rhodium compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
    • C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J2219/24—Stationary reactors without moving elements inside
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/30—Addition reactions at carbon centres, i.e. to either C-C or C-X multiple bonds
    • B01J2231/32—Addition reactions to C=C or C-C triple bonds
    • B01J2231/321—Hydroformylation, metalformylation, carbonylation or hydroaminomethylation
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80—Complexes comprising metals of Group VIII as the central metal
    • B01J2531/82—Metals of the platinum group
    • B01J2531/822—Rhodium
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
    • C07F9/6568—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus atoms as the only ring hetero atoms
    • C07F9/65683—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus atoms as the only ring hetero atoms the ring phosphorus atom being part of a phosphine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
    • C07F9/6568—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus atoms as the only ring hetero atoms
    • C07F9/65685—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus atoms as the only ring hetero atoms the ring phosphorus atom being part of a phosphine oxide or thioxide

Definitions

  • the invention relates to a mixture of unsymmetrical bisphosphites, a process for its preparation, as well as their reaction with metals containing mixtures to complex mixtures of the bisphosphites and the metal, and their use as a catalytically active composition in hydroformylation reactions, as well as the hydroformylation reaction itself.
  • Each catalytically active composition has its specific advantages. Depending on the starting material and target product therefore different catalytically active compositions are used.
  • Catalytically active compositions based on rhodium bisphosphite complexes are suitable for the hydroformylation of linear olefins having terminal and internal double bonds, predominantly terminally hydroformylated products being formed. In contrast, branched olefins with internal double bonds are converted only to a small extent.
  • These phosphites when coordinated to a transition metal center, provide catalysts of increased activity, but the pot life of these catalytically active compositions is unsatisfactory, among other reasons because of the hydrolysis sensitivity of the phosphite ligands.
  • substituted bisaryldiols as building blocks for the phosphite ligands, as in EP 0 214 622 or EP 0 472 071 described significant improvements could be achieved.
  • symmetrically constructed bisphosphites are prepared and used as ligands for hydroformylation.
  • the symmetrically constructed bisphosphite ligands used in the hydroformylation are prepared at low temperatures. Compliance with these low temperatures is imperative because higher temperatures according to these US documents would lead to rearrangements and ultimately to asymmetrically constructed bisphosphites, but this is not desirable here.
  • Bisphosphites disclosed in column 8 under the general formula (V) are symmetrical bisphosphites.
  • the bisphosphite is symmetric even when X 1 and X 2 are different radicals, as shown in the table in column 11 at ref. 2 and 3 is the case.
  • ligands in the hydroformylation reaction are used in the prior art, since the other isomer strong negative influences on the overall performance of the system.
  • the asymmetric isomer would be present as a minor component, since only symmetrical ligands are used in the hydroformylation,
  • WO 2007/149143 describes a mixture of two monophosphites, which is used as an antioxidant for polymer resins.
  • a long service life means that the hydroformylation-active composition comprising the ligands, among other components, has a low tendency to degrade these ligands and / or the decomposition of these ligands into hydroformylation-inhibiting components, such as the so-called "poisoning phosphites" .
  • Both Ia 'and Ia are unsymmetrical, so there is a mixture of two different asymmetric bisphosphites, and unsymmetrical means that if R1 is R3 then R2 can not be R4 at the same time, or just in case in that R2 is R4, R1 can not be R3 at the same time.
  • the content of compound (Ia ') is in a range of 99.5 to 0.5 mol%
  • the content of compound (Ia ") is in a range of 0.5 to 99.5 mol%.
  • the two compounds (Ia ') and (Ia ") add up to 100 mol%.
  • the mixture comprises the compounds Ib 'and Ib ": where M is selected from Fe, Ru, Os, Co, Rh, Ir, Ni, Pd, Pt, and M can make additional bindings, and the compounds (Ib ') and (Ib ") are not identical.
  • the content of the compound (Ib ') is in a range of 99.5 to 0.5 mol%
  • the content of the compound (Ib ") is in a range of 0.5 to 99.5 mol%.
  • the two compounds (Ib ') and (Ib ") add up to 100 mol%.
  • the mixture comprises the compounds Ic 'and Ic ": wherein M is selected from Fe, Ru, Os, Co, Rh, Ir, Ni, Pd, Pt, and and the compounds (Ic ') and (Ic ") are not identical.
  • the content of compound (Ic ') is in a range of 99.5 to 0.5 mol%
  • the content of compound (Ic ") is in a range of 0.5 to 99.5 mol%.
  • the two compounds (Ic ') and (Ic ") add up to 100 mol%.
  • the mixture comprises at least one compound (Ia ') or (Ia ") which are not bound to M.
  • M is Rh.
  • R1 is -Me
  • R3 is not -Me
  • R2 is -Me
  • R4 is not -Me
  • R1 and R2 are -Me.
  • R1 is -tBu
  • R3 is not -tBu
  • R2 is -OMe
  • R4 is not -OMe
  • the bisphosphites have the structures (1Ia ') and (1Ia "):
  • sterically hindered secondary amines are used as further components.
  • composition comprises a previously described mixture which comprises, in addition to the mixture, at least one amine having a 2,2,6,6-tetramethylpiperidine moiety.
  • the amine having the formula (7), sebacic di-4- (2,2,6,6-tetramethylpiperidinyl) ester is preferably used.
  • a particularly preferred metal in the composition of the invention is rhodium.
  • the unsaturated compounds that are hydroformylated in the process of the present invention include hydrocarbon mixtures obtained in petrochemical processing plants. These include, for example, so-called C 4 cuts. Typical compositions of C 4 cuts from which most of the polyunsaturated hydrocarbons have been removed and which can be used in the process according to the invention are listed in the following Table 1 (see DE 10 2008 002188 ). Table 2: Steam cracker Steam cracker Catalytic splitting plant component HCC 4 HCC 4 / SHP Raff. I Raff.
  • the mixture comprises unsaturated compounds having 2 to 30 carbon atoms.
  • the mixture has unsaturated compounds having 2 to 8 carbon atoms.
  • the mixture has polyunsaturated hydrocarbons.
  • the mixture comprises butadienes.
  • the unsaturated compounds which are hydroformylated in the process of the invention further comprise unsaturated carboxylic acid derivatives.
  • these unsaturated carboxylic acid derivatives are selected from fatty acid esters.
  • the multiphase reaction mixture according to the invention comprises at least one unsaturated compound as disclosed above and comprises, in addition to hydrocarbon mixtures derived from steam cracking, catalytically operated cracking or oligomerization processes or other sources of monounsaturated and / or polyunsaturated Carbon compounds or unsaturated carboxylic acid derivatives include at least one hydroformylation product of these unsaturated compounds as listed in the examples below and the particular composition used as previously disclosed.
  • the complex compounds of the formulas (Ic ') and (Ic ") according to the invention are formed in situ during the hydroformylation reaction.
  • the complex compounds (Ic ') and (Ic ") are present in addition to the unbound bisphosphite.
  • the characterization of the hydridocarbonyl complex (Ic ') with rhodium as metal was done by theoretical calculations. The result is in the FIG. 1 shown in the appendix.
  • the structure calculation was performed with the BP86 functional and the def SV (P) basis set.
  • this additionally comprises process step g) reaction with M to give (Ic ') and (Ic "), where M is selected from Fe, Ru, Os, Co, Rh, Ir, Ni, Pd, Pt.
  • the biphenol (3IIIa) used as precursor was prepared according to the following synthesis instructions.
  • Variant 1 ACN / NEt 3
  • the target product could be obtained as a white solid (5.0 g, 58%).
  • Variant 4 Conducting a low-temperature test at -20 ° C
  • the resulting solid was filtered the next morning and washed twice with 5 ml of dried toluene. The resulting filtrate was then concentrated to dryness.
  • the target product could be obtained as a white solid (2.59 g, 71%).
  • the experiments were carried out in 100 ml autoclave from Parr Instrument.
  • the autoclaves are equipped with electric heating.
  • the pressure is maintained by means of mass flow meter and pressure regulator.
  • a precisely defined quantity of starting material can be injected under reaction conditions via a syringe pump.
  • samples can be taken during the experimental period and analyzed using GC as well as LC-MS analysis.

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EP13773210.3A 2012-10-12 2013-09-27 Gemisch aus verschiedenen unsymmetrischen bisphosphiten und dessen verwendung als katalysatorgemisch in der hydroformylierung Active EP2906574B1 (de)

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Application Number Priority Date Filing Date Title
DE102012218629 2012-10-12
DE102012218627 2012-10-12
DE102012218630 2012-10-12
DE102012218625 2012-10-12
PCT/EP2013/070238 WO2014056737A1 (de) 2012-10-12 2013-09-27 Gemisch aus verschiedenen unsymmetrischen bisphosphiten und dessen verwendung als katalysatorgemisch in der hydroformylierung

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EP2906574A1 EP2906574A1 (de) 2015-08-19
EP2906574B1 true EP2906574B1 (de) 2016-11-02

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EP13773204.6A Active EP2906571B1 (de) 2012-10-12 2013-09-27 Unsymmetrisches bisphosphit
EP13766563.4A Active EP2802550B1 (de) 2012-10-12 2013-09-27 Langzeitstabiles verfahren zur herstellung von c5-aldehyden
EP13773208.7A Active EP2906573B1 (de) 2012-10-12 2013-09-27 Gemisch von bisphosphiten und dessen verwendung als katalysatorgemisch in der hydroformylierung
EP13773210.3A Active EP2906574B1 (de) 2012-10-12 2013-09-27 Gemisch aus verschiedenen unsymmetrischen bisphosphiten und dessen verwendung als katalysatorgemisch in der hydroformylierung
EP13773207.9A Active EP2906572B1 (de) 2012-10-12 2013-09-27 Gemische konstitutionsisomerer bisphosphite

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EP13773204.6A Active EP2906571B1 (de) 2012-10-12 2013-09-27 Unsymmetrisches bisphosphit
EP13766563.4A Active EP2802550B1 (de) 2012-10-12 2013-09-27 Langzeitstabiles verfahren zur herstellung von c5-aldehyden
EP13773208.7A Active EP2906573B1 (de) 2012-10-12 2013-09-27 Gemisch von bisphosphiten und dessen verwendung als katalysatorgemisch in der hydroformylierung

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US (5) US9499463B2 (es)
EP (5) EP2906571B1 (es)
JP (5) JP2015536302A (es)
KR (5) KR101717864B1 (es)
CN (5) CN104837853B (es)
AR (4) AR092989A1 (es)
CA (4) CA2887582A1 (es)
ES (4) ES2566069T3 (es)
MX (4) MX2015004613A (es)
SG (5) SG11201502824VA (es)
TW (1) TW201422632A (es)
WO (5) WO2014056735A1 (es)
ZA (4) ZA201503227B (es)

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DE102013217174A1 (de) 2013-08-28 2015-03-05 Evonik Industries Ag Zusammensetzung und deren Verwendung in Verfahren zur Hydroformylierung von ungesättigten Verbindungen
DE102013217166A1 (de) * 2013-08-28 2015-03-05 Evonik Industries Ag Verfahren zur Hydroformylierung von ungesättigten Verbindungen durch SILP-Katalyse
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